3D-QSAR and Docking Modeling Study of 1,3,5-Triazine Derivatives as PSII Electron Transport Inhibitor

Chunling Zhang; Shan Chang; Xuhong Tian; Yuanxin Tian

doi:10.14233/ajchem.2014.15883

Issue

Vol. 26 No. 1 (2014): Vol 26 Issue 1

Issue Published : December 26, 2013

This work is licensed under a Creative Commons Attribution 4.0 International License.

3D-QSAR and Docking Modeling Study of 1,3,5-Triazine Derivatives as PSII Electron Transport Inhibitor

https://doi.org/10.14233/ajchem.2014.15883

Chunling Zhang

College of Information, South China Agricultural University, Guangzhou, P.R. China

Shan Chang

College of Information, South China Agricultural University, Guangzhou, P.R. China

Xuhong Tian

College of Information, South China Agricultural University, Guangzhou, P.R. China

Yuanxin Tian

School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, P.R. China

Corresponding Author(s) : Shan Chang

schang@scau.edu.cn; scauzcl@163.com

Asian Journal of Chemistry, Vol. 26 No. 1 (2014): Vol 26 Issue 1
Article Published : December 27, 2013

Abstract

Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were applied to a set of 38 1,3,5-trazines derivatives herbicide. The comparative molecular field analysis model yielded the leave-one-out (LOO) crossvalidated correlation coefficient (q²) of 0.634 and a non-cross-validated correlation coefficient (r²) of 0.954. Comparative molecular similarity indices analysis model gave q² = 0.679 and r² = 0.924. The results indicate that two models have good predictability. The binding model of 1,3,5-trazines with the D1 protein of PSII was built. The docking studies indicated the F atom on 6-fluoroalkyl could formed the H-bond with NH of the main chain and side chain of His215 on the D1 protein, which could explain fluoromethyl-substituted is very important for strong inhibition and have high activity. The models provide guidance for designing highly active compound of herbicide synthesis.

Keywords

CoMFA CoMSIA 1 3 5-trazine derivatives Herbicide Docking. Docking

Zhang, C., Chang, S., Tian, X., & Tian, Y. (2013). 3D-QSAR and Docking Modeling Study of 1,3,5-Triazine Derivatives as PSII Electron Transport Inhibitor. Asian Journal of Chemistry, 26(1), 264–268. https://doi.org/10.14233/ajchem.2014.15883

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References

Y. Umena, K. Kawakami, J.R. Shen and N. Kamiya, Nature, 473, 55 (2011); doi:10.1038/nature09913.

B. Loll, J. Kern, W. Saenger, A. Zouni and J. Biesiadka, Nature, 438, 1040 (2005); doi:10.1038/nature04224.

W. Oettmeier, Cell. Mol. Life Sci., 55, 1255 (1999); doi:10.1007/s000180050370.

H. Kohno, A. Ohki, S. Ohki, K. Koizumi, M.E. Van den Noort, G.C. Rodrigues, J.J.S. Van Rensen and K. Wakabayashi, Photosynth. Res., 65, 115 (2000); doi:10.1023/A:1006493703939.

I. HEAP, International Survey of Herbicide Resistant Weeds (2002).

K. Koizumi, N. Kuboyama, K. Tomono, A. Tanaka, A. Ohki, H. Kohno, K. Wakabayashi and P. Böger, Pestic. Sci., 55, 642 (1999); doi:10.1002/(SICI)1096-9063(199906)55:6<642::AID-PS991>3.0.CO;2-2.

R. Okano, A. Ohki, S. Ohki, H. Kohno, J.J.S. van Rensen, P. Boger and K. Wakabayashi, J. Biosci., 57, 1009 (2002).

R.D. Clark, Pest Manage. Sci., 68, 513 (2012); doi:10.1002/ps.3256.

R.D. Cramer, D.E. Patterson and J.D. Bunce, J. Am. Chem. Soc., 110, 5959 (1988); doi:10.1021/ja00226a005.

M. Bohm, J. Strzebecher and G. Klebe, J. Med. Chem., 42, 458 (1999).

Sybyl, Molecular Modeling Package, version 7.3, St Louis (MO): Tripos Associates (2000).

J. Gasteiger and M. Marsili, Tetrahedron, 36, 3219 (1980); doi:10.1016/0040-4020(80)80168-2.

M. Clark, R.D. Cramer and N. Van Opdenbosch, Comput. Chem., 10, 982 (1989); doi:10.1002/jcc.540100804.

R.D. Cramer III, J.D. Bunce, D.E. Patterson and I.E. Frank, Quant. Struct. Act. Relat., 7, 18 (1988); doi:10.1002/qsar.19880070105.

A.K. Ghose and G.M. Crippen, J. Chem. Inf. Comput. Sci., 27, 21 (1987); doi:10.1021/ci00053a005.

K.N. Ferreira, T.M. Iverson, K. Maghlaoui, J. Barber and S. Iwata, Science, 303, 1831 (2004); doi:10.1126/science.1093087.

A. Zouni, H.T. Witt, J. Kern, P. Fromme, N. Krauss, W. Saenger and P. Orth, Nature, 409, 739 (2001); doi:10.1038/35055589.

X.F. Han, Y.X. Liu, Y. Liu, L.H. Lai, R.Q. Huang and Q.M. Wang, Chin. J. Chem., 25, 1135 (2007); doi:10.1002/cjoc.200790212.

Issue

Vol. 26 No. 1 (2014): Vol 26 Issue 1

3D-QSAR and Docking Modeling Study of 1,3,5-Triazine Derivatives as PSII Electron Transport Inhibitor

Corresponding Author(s) : Shan Chang

Abstract

Keywords

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